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Literature DB >> 21291216

Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters.

Alexandre Lumbroso¹, Philipp Koschker, Nicolas R Vautravers, Bernhard Breit.

Abstract

A new method for the preparation of a wide range of branched allylic esters from terminal alkynes that proceeds via a redox-neutral propargylic CH activation employing a rhodium(I)/DPEphos catalyst is reported.

Entities: Chemical

Mesh：

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Year: 2011 PMID： 21291216 DOI： 10.1021/ja1108613

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

13 in total

1. Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors: Jiajie Feng; Michael Holmes; Michael J Krische
Journal: Chem Rev Date: 2017-09-14 Impact factor: 60.622

2. Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Authors: Qing-An Chen; Zhiwei Chen; Vy M Dong
Journal: J Am Chem Soc Date: 2015-06-29 Impact factor: 15.419

3. Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors: Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal: J Am Chem Soc Date: 2017-07-25 Impact factor: 15.419

Review 4. Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors: Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2017-08-10 Impact factor: 15.336

5. Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

Authors: Qing-An Chen; Faben A Cruz; Vy M Dong
Journal: J Am Chem Soc Date: 2015-01-21 Impact factor: 15.419

6. Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

Authors: Tao Liang; Wandi Zhang; Te-Yu Chen; Khoa D Nguyen; Michael J Krische
Journal: J Am Chem Soc Date: 2015-09-29 Impact factor: 15.419

Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters.

1. Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

2. Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

3. Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Review 4. Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

5. Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

6. Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

7. Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

8. Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

9. Catalytic asymmetric synthesis of geminal-dicarboxylates.

10. Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.